Chesapeake Bay Sailors' Favorite Cruising Anchorages

Favorite Chesapeake Bay Anchorages (Don’t Tell Everybody)

We asked SpinSheet cruising sailors to share some of their favorite Chesapeake Bay anchorages, and the top answer was “don’t tell everybody.” We all like to think our favorite hidey hole is a secret, yet the reality for many sailors is that we tend to regularly drop the hook in places we can easily get to and back from over the weekend; many of those places were discovered by Captain John Smith and have been “secrets” shared many times over 400 years. 

We sailors help one another by sharing the places we love, both by talking about them with fellow cruisers and by physically sharing the anchorage. In that spirit, discover some well-loved anchorages below. 

Chester River

Reeds Creek
Cruising sailors savor sunrises and sunsets on the hook. Photo by Eva Hill

Reed Creek
SpinSheet contributor Eva Hill likes Reed Creek off the Chester. She says, “It’s mostly nettle-free in the summer. Quiet, because it looks like it’s hard to get to. Open to breezes.”
Langford Creek
Members of the Rock Hall Yacht Club will tell you why they love their scenic and winding creek with many anchoring options to explore. 

Miles River 

St. Michaels
A furry friend brightens up any cruise for most sailors. Photo by Scott Gelo​​

St. Michaels
Scott Gelo, who cruises with his wife Jennifer Bickford and their dog, says, “We absolutely love St. Michaels. On the Miles River side of the town (main entrance), there are two anchorages that we always squeeze into. One is the bight just inside Parrott Point across from the Chesapeake Bay Maritime Museum, and the other is off the Inn at Perry Cabin on the opposite side of the museum. 

“Both anchorages are neat in their own respects. It is quieter on the Perry Cabin side; you get a grand view of the inn, and there is a lot more space. The bight offers views back into town and what seems to be an endless boat parade that you have a front row seat to.” 
Wye River
Some sailors sail up Eastern Bay and right past this peaceful river en route to St. Michaels without ever exploring the wild and winding Wye. 

Shaw Bay
Sailors who frequent Shaw Bay know the sunsets are spectacular. Photo b Jeffrey Thompson

Shaw Bay 
Shaw Bay is the easiest Wye anchorage to get to, as it’s just to the right after entering the Wye. One of its claims to fame is what happens there the weekend after Labor Day: the Eastport Oyster Boys play an on-water concert from a boat to 80-plus boats to benefit ShoreRivers programs. 
Dividing Creek
Jesse Falsone says about Dividing Creek, “Peaceful, beautiful, and a fun trip there.” 

Ross Weintraub first stayed there in the mid-70s during a hurricane. “(It’s a) great hurricane hole," he says. “Also, a good crabbing spot and offers quick access to St. Michaels.” 

It’s worth noting that you may paddle to the Wye River Natural Resources area from this creek—our editor saw a great horned owl there! Dividing Creek is not a secret, so arrive early and rest assured that there are other nearby and well-protected anchorages up the East Wye River. 

Choptank River

San Domingo Creek
Gelo says, “San Domingo Creek off the Choptank River is the ‘back door’ to St Mikes and offers a completely different vibe from the others. If you are after tranquility, this is the spot. After passing a few small sandy islands that usually have bald eagles on them, you enter San Domingo’s main anchorage area. Nice homes on the shoreline in a very quiet setting and the brand new dinghy dock a small dinghy ride up the creek drops you off at the base of W Chew Avenue, giving you easy access to town.”

Cruising sailors relish peaceful evenings and quiet mornings. LaTrappe Creek. Photo by Scott Gelo

LaTrappe Creek
Gelo says of La Trappe Creek, “We like to anchor right off the sandbar that is to port once you enter the creek. The entrance almost feels like New England with the large lighthouse-esque navigation buoys that you must snake around to stay in the channel. We love this anchorage because the sandbar is massive and a great place to land with your dog. It drops off to roughly 10 feet deep right off the beach, so during the day on weekends it is very crowded with powerboats of all sizes beached on it, most of which leave around dusk but the anchorage can still be pretty crowded. 

“For those who like a more tranquil setting, I would advise to either come during the week or head farther up the creek away from the main anchorage, though we have never done that since we enjoy the scenery so much.”

Potomac River

Smith Creek

Smith Creek
Smith Creek, off the Potomac River. Photo by Scott Gelo

Gelo adds another favorite: “Smith Creek is just before the St. Mary’s River on the north side of the Potomac soon after entering the river. The spot we like the best is only big enough for one or two boats and has a nice sandy beach to land with your dog. Like LaTrappe Creek, you can anchor very close to the beach since the depth drops rapidly. Farther up the creek is a larger anchorage, but if you are lucky to grab this one, it is sure a treat with a protected cove and beach all to yourself.”

Rappahannock River

Little Bay
Clark Dennison, who sails with his partner Jenny Holzer, says, “I would say our favorite is Little Bay tucked behind Windmill Point (just north of the Rap), providing coverage from southerly or easterly breezes. You can drop your hook and walk the beach around the island or paddleboard through Civil War-era channels used as an avenue to run Confederate blockade runners. On Sunday, the beach fills up with locals for a Sunday-Fun-Day. The pictures do not do the place justice. Wish I had more of the beach.”